N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide

Base Information

• Chemical Name: N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide
• CAS No.: 815581-41-0
• Molecular Formula: C₃₇H₅₁N₅O₇
• Molecular Weight: 677.841
• Mol file: 815581-41-0.mol

Synonyms:

Chemical Property of N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide

There total 12 articles about N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-benzyloxyamine (622-33-3) → N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide (815581-41-0)

Guidance literature:

Multi-step reaction with 11 steps

1: DIEA / methanol

2: trifluoroacetic acid

3: acylase

4: Et₃N

5: DCC; DMAP

6: trifluoroacetic acid

7: HBTU; HOBt*H₂O; Et₃N

8: TBAF / tetrahydrofuran

9: trifluoroacetic acid

10: HATU; DIEA / dimethylformamide

With dmap; acylase; tetrabutyl ammonium fluoride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.03.018

Reference yield:

N-formyl-N-benzyloxyamine (183991-46-0) → N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide (815581-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 25 percent / KI; K₂CO₃ / acetone / 36 h / Heating

2: trifluoroacetic acid

3: HBTU; HOBt*H₂O; Et₃N

4: TBAF / tetrahydrofuran

5: trifluoroacetic acid

6: HATU; DIEA / dimethylformamide

With tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2004.03.018

Reference yield:

N-acetyl-DL-7-bromoheptanoic acid (669091-26-3) → N-Benzyloxy-N-{5-[(6S,9R,12S,14aR)-6-((S)-sec-butyl)-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-pentyl}-formamide (815581-41-0)

Guidance literature:

Multi-step reaction with 12 steps

1: DMAP

2: DIEA / methanol

3: trifluoroacetic acid

4: acylase

5: Et₃N

6: DCC; DMAP

7: trifluoroacetic acid

8: HBTU; HOBt*H₂O; Et₃N

9: TBAF / tetrahydrofuran

10: trifluoroacetic acid

11: HATU; DIEA / dimethylformamide

With dmap; acylase; tetrabutyl ammonium fluoride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.03.018

upstream raw materials:

(S)-2-[(1-{(2S,3S)-2-[(R)-2-Amino-3-(4-methoxy-phenyl)-propionylamino]-3-methyl-pentanoyl}-piperidine-2-carbonyl)-amino]-7-(benzyloxy-formyl-amino)-heptanoic acid

N-benzyloxyamine

N-formyl-N-benzyloxyamine

N-acetyl-DL-7-bromoheptanoic acid